Photoredox-Catalyzed C–H Functionalization Reactions

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 1925 - 2016

Published: Sept. 29, 2021

The fields of C–H functionalization and photoredox catalysis have garnered enormous interest utility in the past several decades. Many different scientific disciplines relied on strategies including natural product synthesis, drug discovery, radiolabeling, bioconjugation, materials, fine chemical synthesis. In this Review, we highlight use reactions. We separate review into inorganic/organometallic catalysts organic-based catalytic systems. Further subdivision by reaction class─either sp2 or sp3 functionalization─lends perspective tactical for these methods synthetic applications.

Language: Английский

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Visible light photocatalysis in the late-stage functionalization of pharmaceutically relevant compounds

Chemical Society Reviews, Journal Year: 2020, Volume and Issue: 50(2), P. 766 - 897

Published: Dec. 22, 2020

Recent developments and future prospects of visible-light photocatalysis in the late-stage functionalization pharmaceuticals natural bioactive compounds.

Language: Английский

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Mechanochemistry: New Tools to Navigate the Uncharted Territory of “Impossible” Reactions

ChemSusChem, Journal Year: 2022, Volume and Issue: 15(17)

Published: July 21, 2022

Mechanochemical transformations have made chemists enter unknown territories, forcing a different chemistry perspective. While questioning or revisiting familiar concepts belonging to solution chemistry, mechanochemistry has broken new ground, especially in the panorama of organic synthesis. Not only does it foster "thinking outside box", but also opened reaction paths, allowing overcome weaknesses traditional exactly where use well-established solution-based methodologies rules out progress. In this Review, reader is introduced an intriguing research subject not yet fully explored and waiting for improved understanding. Indeed, study mainly focused on that, although impossible solution, become possible under mechanochemical processing conditions, simultaneously entailing innovation expanding chemical space.

Language: Английский

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Enroute sustainability: metal free C–H bond functionalisation

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(7), P. 2391 - 2479

Published: Jan. 1, 2023

The metal-free C–H functionalisation is providing environmentally benign, cost-effective, sustainable catalytic systems. Comprehensive developments of various reactions are the focal point this review.

Language: Английский

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BI-OAc-Accelerated C3–H Alkylation of Quinoxalin-2(1H)-ones under Visible-Light Irradiation

Organic Letters, Journal Year: 2020, Volume and Issue: 22(15), P. 5984 - 5989

Published: July 24, 2020

An efficient, photoredox-catalyst-free radical alkylation of quinoxalin-2(1H)-ones has been described. This reaction utilizes 4-alkyl-1,4-dihydropyridines (R-DHPs) as alkyl precursors and acetoxybenziodoxole (BI-OAc) an electron acceptor to undergo single-electron transfer with photoexcited R-DHPs. The benign conditions allow for good compatibility in the scope both synthetic value protocol was also demonstrated by successful functionalization natural products drug-based complex molecules

Language: Английский

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N‐Centered Radical Directed Remote C−H Bond Functionalization via Hydrogen Atom Transfer

Chemistry - An Asian Journal, Journal Year: 2020, Volume and Issue: 15(6), P. 651 - 672

Published: Feb. 3, 2020

The N-centered radical directed remote C-H bond functionalization via hydrogen-atom-transfer at distant sites has developed as an enormous potential tool for the organic synthetic chemists. Unactivated and secondary tertiary, well selected primary bonds, can be utilized by following these methodologies. synthesis of heterocyclic scaffolds provides them extra attention modern days' developments in this field unactivated bonds functionalizations.

Language: Английский

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Visible-Light-Enabled Ortho-Selective Aminopyridylation of Alkenes with N-Aminopyridinium Ylides

Journal of the American Chemical Society, Journal Year: 2020, Volume and Issue: 142(28), P. 12420 - 12429

Published: July 2, 2020

By utilizing an underexplored reactivity mode of N-aminopyridinium ylides, we developed the visible-light-induced ortho-selective aminopyridylation alkenes via radical-mediated 1,3-dipolar cycloaddition. The photocatalyzed single-electron oxidation ylides generates corresponding radical cations that enable previously inaccessible 1,3-cycloaddition with a broader range alkene substrates. resulting cycloaddition adducts rapidly undergo subsequent homolytic cleavage N-N bond, conferring substantial thermodynamic driving force to yield various β-aminoethylpyridines. Remarkably, amino and pyridyl groups can be installed into both activated unactivated modular control ortho-selectivity 1,2-syn-diastereoselectivity under metal-free mild conditions. Combined experimental computational studies are conducted clarify detailed reaction mechanism origins site selectivity diastereoselectivity.

Language: Английский

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Green chemistry meets medicinal chemistry: a perspective on modern metal-free late-stage functionalization reactions

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(19), P. 10955 - 10982

Published: Jan. 1, 2021

This review summarizes the most recent advances of metal-free late-stage functionalization (LSF) pharmaceutically relevant molecules. Particular emphasis is placed on C – H activation as well use endogenous functional groups.

Language: Английский

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Site-selective remote C(sp3)–H heteroarylation of amides via organic photoredox catalysis

Nature Communications, Journal Year: 2019, Volume and Issue: 10(1)

Published: Oct. 18, 2019

Radical translocation processes triggered by nitrogen-centered radicals (NCRs), such as 1,5-hydrogen atom transfers (1,5-HAT), demonstrated the well-established Hofmann-Löffler-Freytag (HLF) reaction, provide an attractive approach for controllable and selective functionalization of remote inert C(sp3)-H bonds. Here we report amidyl radical-triggered site-selective heteroarylation amides under organic photoredox conditions. This provides a mild highly regioselective reaction affording heteroarylated at room temperature transition-metal free, weakly basic, redox-neutral Non-prefunctionalized heteroarenes, purines, thiazolopyridines, benzoxazole, benzothiazoles, benzothiophene, benzofuran, thiazoles quinoxalines, can be alkylated directly. Sequential orthogonal C-H different heteroarenes taking advantage pH value or polarity has also been achieved. DFT calculations explain predict site-selectivity reactivity this reaction. strategy expands scope Minisci serves its alternative potential complement.

Language: Английский

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Radical Functionalization of Remote C(sp ³ )–H Bonds Mediated by Unprotected Alcohols and Amides

CCS Chemistry, Journal Year: 2020, Volume and Issue: 2(5), P. 813 - 828

Published: June 10, 2020

Aliphatic alcohols and amides are highly valued, ubiquitous chemicals in synthetic chemistry. Radical-promoted regioselective functionalization of unactivated C(sp3)–H bonds offers an atom step...

Language: Английский

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